


Ace Up His Sleeve

by Kimyōna Akage 奇妙な赤毛 (kheradihr)



Category: Original Work
Genre: Anal Fingering, Anal Sex, Blow Jobs, Casinos, Elevator Sex, M/M, bubble bath sex, cross dressing
Language: English
Status: Completed
Published: 2016-03-06
Updated: 2016-03-06
Packaged: 2018-05-25 01:26:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,438
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6174763
Author URL: https://archiveofourown.org/users/kheradihr/pseuds/Kimy%C5%8Dna%20Akage%20%E5%A5%87%E5%A6%99%E3%81%AA%E8%B5%A4%E6%AF%9B
Summary: <blockquote class="userstuff">
              <p>What should be a regular night for casino muscle Bert and Ishmael becomes exactly the opposite when their boss' son tries to humiliate a coworker.</p>
            </blockquote>





	Ace Up His Sleeve

It was all Frankie's idea. If it were up to me and Ishmael, none of this would've happened.

Okay, maybe it would've happened, but it wouldn't've happened in a way that we knew about.

It was a usual Tuesday night in the casino, money was flowing and the lights were bright. Ishmael -- the crew calls him Mael but it doesn't suit him – and I were walking the floor over by the blackjack tables keeping an eye on the girls. Tuesday nights were the nights the boss scheduled the real pretty girls to get money in since it's so slow usually. Our boss doesn't like scheduling a lot of girls on the weekend since the drunks tend to get handsy. After one of the girls pulled out a hair stick and stabbed a customer for copping a feel, that policy went into effect real fast. We like our girls feisty, but stabbing idiots hurts business.

Connie over at the blackjack tables reached up to her impeccably tight French twist and tucked a nonexistent stray lock back into her 'do. The tacky, blocky costume jewelry bracelet on the moving hand winked in the lights. That was the signal. Someone at her table was raking in the money a little too well. Truth be told, we don't really care how he was doing it -- counting cards, got something up his sleeve, even Lady Luck blowing him under the tables -- but the man was done. Casinos existed to make money for the people that ran them, not the people that played in them. I shifted closer to the tables to get a scope on things while Ishmael called in the calvary. I could hear him through the earpiece.

_"This is Ishmael. Connie at Table Eight has got someone on fire. Can we get some back-up here?"_

_"That true, Bertrand?"_ I never let it show on my poker face but I fucking hate it when Frankie calls me by my full name. He's the only one who does it because he knows I can't dent his face without denting my paycheck. It was also a known secret that he doesn't trust his daddy's men and we don't trust him. _"We got ourselves a cheat?"_

"Cheat or no, he's got what looks like twenty thou won so far."

_"Shit. I'll get the Kid."_

I don't know where we got the Kid but he was our trump card. Any time someone was getting lucky at the tables we would send him in to clean up and clean out any competition. Interesting thing about him was he'd do it in a way that you didn't realize you were losing your money faster than a sliced artery pumping blood out until you put down the last chip. Even then, whoever he just beggared never took it hard. Boss said he was lucky and took good care of him. I met him a few times and figured if he weren't a fuckstick like Frankie I could tolerate him. Besides, the Kid kept to himself most of the time. He knew his place and stuck to it.

It wasn't long until I heard the private elevator ding and a quiet voice in my ear. _"‘Evening, Bert."_

I nodded to the Kid. "Owen."

_"I see Ishmael is working tonight. Give him my regards, will you?"_ he asked as he lifted two fingers to salute Ishmael across the floor even though he knew Ishmael could hear him over the comms.

"I will," I promised him. Besides, it was worth the smile I got out of Ishmael every time I passed along the message.

He touched his temple in a quick salute before heading over to the tables. If he weren't indoors he'd tip his hat. That was how Owen was: dapper and chivalrous, which was why Frankie hated him. Owen was old-school classy in a way that Frankie tried, failed and managed to look skeevy while doing.

"Is there anything I should know?" Owen asked halfway down the carpet. He was drawing a few eyes from the slot machines but even his face couldn't distract them from missing their pull. Slot players were nearly as mechanical as the machines they played.

"He likes to go all in a lot. Connie's starting to get angry."

He chuckled. "Then I'll go do my best to get Connie all of her money back."

Before I could wish him luck he pulled the earpiece out and let it fall inside his shirt. He never worked with someone in his ear. Lucky bastard.

As he sat down at the table Ishmael and I switch out with the other pair working our area and headed to the video room for a much needed coffee and seat. Frankie was in there so we nodded and got our coffee. When we sat we end up staring at the wall of screens that make up the room. Each area of the casino floor was on display, with the big TV running the camera near Connie's table. It was nice and quiet, a typical night on the casino floor, until Frankie opened his mouth.

"How long you think it'll take for the Kid to clean him out?"

Ishmael shot me a look full of I-don't-like-this before answering. "If he plays it like he usually does, maybe an hour."

Frankie grinned meanly. "That'll work pretty good then."

I drank my coffee to try to keep my comments to myself. I wanted to keep my typical, quiet night to stay typical and quiet. Ishmael was starting to look worried.

"Boss..."

"It's nothing mean, Mael. I just got him something to thank him for all the hard work he does."

Ishmael sat back and drank his coffee slowly, unhappy. Frankie didn't have a single nice bone in his body and we were stuck in the video room with him for the rest of the night. At this point, whatever he got up to, our asses were going to be in a sling with him. Pouring more coffee, we got comfortable and kept watching the monitors.

We watched Owen clean the guy out. He started with small wins while making small talk about how he was new to the city, looking to make it big. As usual, the mark joined in the conversation, telling him as long as he played it smart he'd do well. And that's exactly what Owen did. Making it look like Owen was young and green endeared him to the guy at the table. All the while the mark's chip towers were shrinking.

Owen was down to the mark's last few chips when _she_ came in.

She was a dream floating in on what should have been eye-wateringly high white peep-toe heels. But she made it seem like she was walking in flats. Her movement was probably accentuated by the dress she wore. Our casino is pretty classy and we see all sorts of women coming in and out in all sorts of dresses, but none of those could dream of being like her.

The white dress was two halves, like a clamshell with lacing keeping the dress on her. Silver snaps started at the peak of each breast and stopped right where her nipples would be. Beading trailed down her torso like ghosts of buttons, only to turn back into silver snaps that vanished into her skirt. I'd bet a hundred easy that when she unbuttoned them her panties were visible.

If she was wearing any.

She was the most expensive-to-look-at hooker I'd ever seen and she was heading for Owen, skirt floating like sea foam.

I still don't know where she managed to grab them, but she set a glass of champagne on Owen's cards, somehow shifting them apart. He shot a look at her, eyes wide. She smiled, flashing white teeth at him through a sip of her own glass of champagne.

"He'll double down," she said to Connie, not breaking eye contact with Owen. "Won't you, handsome?"

"You heard the lady, double down. All in."

"What?" Ishmael coughed through his coffee as the mark exclaimed the same thing.

"Lady Luck demands I finish the game." Owen grinned as his free arm wrapped around the hooker's waist. She leaned in and Frankie smiled. "And finish I will."

Owen cleaned the mark out and flipped a 500 chip to Connie before offering his elbow to the hooker and leading her to the private elevators.

"Horny bastard isn't wasting any time," Frankie crowed, leering at the screen. "Wait until he sees the surprise."

I frown. I knew Frankie had something mean planned. "I thought she was the surprise."

He snorted. "It hasn't even started. Now shaddap and watch the show."

I leaned back and put my eyes on the screen, doing my best to ignore Ishmael's foot kicking mine. Yeowza. They were already going at it in the elevator, the hooker loosening Owen's tie as he ruined her slicked forward pixie cut. He moaned something into her mouth and her leg curled up and over his hip. Of course she wore a garter belt to hold up her hose. She was the real deal. Real fucking expensive. I winced at the thought of Benny, our accountant, getting the receipt for this. Poor thing would blow a gasket and then show Big Frankie.

Owen took his time getting on his knees, planting kisses down Lady Luck's neck and leaving pink marks against her pale skin. He never got as far as he planned because each time he made her arch and groan she yanked him up for another kiss. With a handful of her ass and a desperately murmured, "Baby, _please_ ," she finally let him drop to his knees. He nosed at her crotch, her handkerchief skirt somehow hiding the show.

I somehow tore my eyes away from them to look at Frankie. He was livid. I couldn't figure out why and then promptly forgot why I cared. Lady Luck's voice broke mid-moan and I couldn't look away from them.

Owen's throat and a corner of his jaw working was all we could see, but the way she was trying to scale him was proof of how well he was working her. Her legs were wrapped around his head and she was holding herself up on the railing attached to the wall.

"I-inside," she gasped, freeing a hand to tug at his hair. He pulled away and eyed her, lips swollen and slick.

"You sure?" He checked the elevator screen. It read floor 57. Private penthouses were on 78. "We're halfway—"

Her hand tightened until his face was angled uncomfortably and yet still meeting her eyes. "Two fingers inside me now."

I swear, I could almost hear his eyes dilate. Without a word he dove under her skirt, fingers playing at the juncture between her thighs. His wrist cocked forward and slid upward. She gasped, hands reaching to grasp the soundproofing panels on the wall and arched like a bowstring drawn.

Pink nipples popped free of the bodice.

She was a _he_.

There was no way to mistake Lady Luck's – no, _Lord_ Luck's sex with his chest heaving with stuttered gasps as Owen worked two fingers inside him and his nipples caught the bust line of the dress, a perpetual tease.

Things slotted into place once my brain restarted. Frankie tried to screw over and embarrass Owen by getting a hooker in drag to seduce him, except Owen had no problems with men in stunning dresses and impressive shoes. No problems at all, judging by the way he was working Lord Luck's ass as he once again took his cock deep in his throat. My brain ground down to a halt as I realized that Owen was deep-throating him like a pro and with a lot of familiarity with all of Lord Luck's sweet spots.

The _ding!_ of the elevator's hitting the 78th floor startled all of us. Ishmael looked at me, sheepish with dull red cheeks, as Lord Luck let his legs down and Owen extricated him from the dress. Lord Luck's dress was tented prominently. We all squirmed in our seats.

They fell into each other the moment the door shut. I knew that there were cameras in the private suites and I knew that we were breaking the privacy clause of Owen's contract – it's a part of everyone's contract if they take housing in the hotel – but we couldn't look away. They moved together, kissing every piece of exposed skin as Lord Luck quickly got Owen out of his suit, pieces flying all over the room as they moved towards the bathroom. There was a bubble bath there, most likely still hot from the internal heater. The bathtubs in the room were pretty much Jacuzzis with timed baths and regulated temperature.

Suddenly Lord Luck, who was propped on the counter, pushed Owen away with a heeled foot. Owen whined.

"Come on, babe. A quick tumble in the bath won't take too long."

"Not in this dress."

"I can buy you a new one."

"Owen, this one's couture and for tonight only."

Owen wilted and leaned in to try to nuzzle his neck. "Shit, I forgot. We can get a bath later."

"Pssht. Just help me out of the dress." Lord Luck offered one of his feet. "With your teeth, preferably."

Owen couldn't manage unbuckling the shoes with his teeth but he did pop each garter with his teeth, delicately grasping Lord Luck's hose with his front teeth and pulling them off with just a bare whisper of the fabric. He popped the buttons at the base of the corset open to reach inside and pull of his panties. White. Silk and lace, the type to cover everything while hinting at treats beneath. If Lord Luck never spoke, I would think that was all he was made of from his hair to his painted toenails. Soft and delicate, easy to dirty.

He was impatient too. As Owen was taking his time teasing off both his panties and the garter belt he's already unlacing one side of the dress. It peeled off much like his hose did. Naked, he dove for Owen, knocking them into the tub, a tsunami of bubbles drowning the bathmat. There was some wriggling before a wet pair of male underwear smacked the tile floor.

Finally completely naked and dress safely on the counter, the pair pressed their chests together and rolled.

It was like watching the ocean roll perpetually, each movement triggering a successive motion until there was no way to tell when one started and ended. Wholly in synch with each other, I watched wondering what their hands were doing below the bubbles. Were they rubbing against each other, the soapy water giving enough lubrication to move in such a sinuous curve, or was it mutual handjobs, strokes setting the pace for the sloshing of the tub? A sudden shriek and Lord Luck slipped under the bubbles only to come up a moment later spitting and spluttering, make-up ruined answered my question. No hands, just two bodies that knew each other well moving together. A weight sat in the pit of my stomach as I watched Owen wipe the running mascara from under his eyes tenderly.

"I think the bed would be a good idea," he suggested with a little laugh in his voice. Lord Luck nodded and they made their way to the bed, still kissing and stroking each other.

At the edge, Owen took Lord Luck by the waist. But instead of having him climb him like a tree, Owen lifted and threw him easily onto the bed. Lord Luck bounced twice before looking at him. Owen crawled onto the bed to join him, straddling his chest. We couldn't see from the angle of the camera, but it looked like Owen took himself in hand. It was Lord Luck's turn for his eyes to dilate audibly. He reached behind the pillow he was on as Owen crawled even further up until he was straddling Lord Luck's shoulders.

The slap of buttons and swearing pulled me away from the screen long enough to see Frankie trying desperately to find an angle so we could see what was going on. The big screen split into two views, one of Owen's back as he moved and the other of Owen fucking Lord Luck's face. It was strange to see both angles, but it let us watch not only the show but what Lord Luck was doing as Owen rode his face.

Two fingers, slicked with lube, worked along Owen's crack and teased their way in, one after the other in surprisingly coherent motions as if he weren't otherwise occupied. He worked them counter to the rhythm Owen had, pulling breathy moans and something like keening from him until Owen impaled himself on Lord Luck's fingers in a hasty move to pull out of his mouth. The suction breaking made a pop that reverberated in the quiet room.

"Keith," Owen panted, still rocking back on the fingers inside him. "Too much. I ne—heed—"

"Shh," Keith crooned as he eased his fingers out of Owen. "Just go back a few more inches, there, babe, I've got you, just let me." These murmurs continued as Keith coaxed Owen to scoot back far enough to line his hole with Keith's cock. As Owen rocked slowly down on Keith's cock, the murmurs stuttered out to gasps and a groan as Owen bottomed out.

For a moment there was no movement. Then tiny tremors shook Keith's thighs, the only evidence that he was holding back. Muscle twitched and bunched under his skin until he bucked, driving his cock even further into Owen. Owen ground down and back against the thrust. Like the tide following the moon, they moved over and over until there was nothing but their bodies in a perpetual pattern, each breaking against the other. Watching them I wondered if I was staring at the ocean on the beachfront side of the casino rather than the penthouse suite atop it. Then a storm broke.

Like the summer squalls that hit the area with nothing but a gust of wind as warning, Keith and Owen's pace changed with simultaneous motion. Owen curled towards Keith as Keith's hand's found Owen's hips and drove upward, hard. Owen's choked cry was doused as he hauled Keith upward for a kiss, the only kindness amidst the violence of the thrusts. One hand held the back of Keith's neck as the other reached downward, taking himself in hand again and fisting erratically. There was a muffled shout and Owen came, spatters of come landing on Keith's chest. He slumped down as Keith slammed into him, once again going into that comforting mantra. One last thrust and suddenly Owen arched backwards like a drawn bow, cock bobbing half hard as Keith ground out his own orgasm.

They moved slowly after, Keith coaxing Owen to lay out and relax, a soothing hand running over his hip and sneaking between his legs. When Owen flopped onto his back and slowly turtle-rolled to the other side of the bed where the phone was Keith pulled himself out of bed to saunter back to the bathroom. A stray camera watched Keith clean himself off and dress, idly stretching as he put a fresh pair of hose on and buckling up those peep-toed heels. Owen was on the phone and angry despite the blissed-out orgasm glow he still had.

"Boss, my contract says no hookers, and yet my partner was clearly bought while in costume before a show to try to humiliate me." He paused to kiss Keith good-bye as the white fairy pranced out of the suite, off to whatever show he was performing at. "You better find the fuckstick who thought this would be funny and inform him that I don't do hookers and my partner sure as hell isn't one. If you don't, I'm out."

He hung up and flopped back out onto the bed spread eagle as Frankie, sporting a hard on and an embarrassed flush cut the feed. The phone rang.

Ishmael got to it first.

"Yes, sir. We are aware. We'll be there shortly." Hanging up, he stretched a mean grin of his own on his face. "Boss is calling for us Bert. Looks like we get to call it a night early, Frankie."

With a nod to the future target of our boss' rage, I followed Ishmael out, watching him walk ahead of me. Good thing Frankie pulled this. I have some new ideas I can't wait to try out on Ishmael tonight.


End file.
